It's the Most Miserable Time of the Year
by oceannstarr
Summary: May and her friends come to Gem City where she and Ashley will participate in the annual Christmas Contest. The story is much better than this summary. Please Read and Review.AAMAYL AshxMay
1. Chapter 1

It's the Most Miserable Time of the Year

As our heroes continue their journey with their new friends Lauren, Ashley, and Miley to their next location Gem City May and Ashley will face off against each other in the Gem City Christmas Contest.

"Wow this is great I am so excited for the Christmas Contest!" Ashley said. "I just hope that you're ready for this contest May, after all if we are going to be rivals I want you to be at your very best."

"Oh don't worry Ashley I'm ready," May said.

"This will be interesting to see how well these two compete against each other," Lauren said. "Since Miley and I have been with Ashley and helping her prepare for this I haven't seen your abilities May and how you'll perform against my sister."

"Well I've been watching May train and I think she is gonna win that ribbon." Ash said putting his arm around his new girlfriend and giving her a kiss on the cheek. May responded by turning to Ash and pulling him into a kiss. Soon enough they were making out in front of everyone.

"Oh this is just great," Max said impatiently. "I'm happy for my sister but this is ridiculous." Then he turned to look at Miley and her sisters. "You guys just had to make them a couple didn't you?" The three of them laughed and explained that his sister and Ash were just such so cute together that they had to set them up.

"Anyway I think that we should get going if we want to be there before dark." Brock said. Everyone agreed and they were on there way.

Once they got there they couldn't believe their eyes.

"Wow this is the most beautiful town I have every seen," Miley said.

"Yeah it's so colorful and festive. Its towns like this that really make you get into the Christmas spirit." May said her eyes sparkling at the town's beauty. They were right this town was beautiful, every corner, building, and house was decorated with beautiful decorations. In the center of town there was an enormous stunning Christmas tree that was so tall that you could barely see the top of it. It had giant glass ornaments of every color all over it, some were angels others were in the shape of reindeer or snowflakes; on the top of the tree was a massive star.

"Wow that's got to be the biggest tree I have ever seen," Ash said as he gazed up at the tree admiring its beauty. "This will a great place for you two to have your pokemon contest," he said looking at Ashley and May.

"It says in the guide book that Gem City is famous for its holiday decorations and the tree in town square is their oldest tradition here. They spend two weeks decorating the tree and that after the Christmas Contest the whole town comes to the Star Lighting Ceremony were they light the star at the top of the tree and also honor the champion of the Christmas Contest." Brock said.

"Wow that star lighting ceremony sounds so cool," Miley said.

"Hey if you guys don't mind could we head over to the contest hall and register for the Christmas Contest." Ashley said.

"Sure the sooner you guys register the sooner we can go eat." Lauren said.

"I heard that," Ash said. "Let's go guys."

Once they made it to the contest hall Ashley and May register and were ready to go.

"Hey look its May Maple," a voice said from across the room. May turned around and saw a blonde haired girl coming towards her.

"Hello do I know you?" May asked confused she didn't recognize the girl and wondered how she knew her.

"No but since you responded I'm guessing that you are in fact May Maple."

"Yes I am." May said.

"Oh I'm Amber Mason, I've heard about you. I heard your nice, you have no talent and you couldn't win a pokemon contest to save you're life but you're nice." She said smiling deviously.

"Oh yeah and just where have you heard that stuff from," May said fuming.

"Well actually I have watched some of your contests and from what I saw you were terrible, but from what my cousin Drew tells me about you that helped shape my opinion." She said.

"Oh of course Drew is your cousin well for your information I have won my fair share of contests."

"Whatever, but you're not planning on entering this contest are you?"

"As a matter of fact I am." May said.

"Why embarrass yourself because you're obviously going to lose…to me."

"Do flatter yourself I'll win that ribbon, you'll see."

"Well you can keep living in that little dream world of yours and I'll be winning that ribbon. Later May," she said as she walked away leaving May fuming.

_I'll show you little miss perfect just wait. _May thought as she joined back with her friends outside the contest hall.


	2. Chapter 2

After everyone left the contest hall they all went to the pokemon center.

"May are you okay," Max asked. "I mean you haven't said much since we left the contest hall."

"Yeah are you feeling okay?" Ash asked concerned for his girlfriend, noticing that she wasn't acting like herself.

"I'm fine you guys I guess I'm just tired," May said. But what was really bothering her was Amber. She kept thinking about her encounter earlier that day with her. _I would love to put Amber in her place and beat her sorry butt in the Christmas Contest coming up. _May thought.

Ash had trouble believing her. _I wonder why May won't tell me what's wrong. I can tell something's bothering her, oh well maybe I am wrong she could be tired. We did have a long day today. _Ash tried to shake the thought but he couldn't. _I know what I can do to help her feel better! _Then he realized that everyone else went off without him. After everyone had dinner some evening training and then headed off to bed.

Yawn "I'm really tired I need sleep," May said drifting off to sleep.

_"Next let's welcome May from Petalburg City," Marilyn Meridian, the MC of the contest said. _

_"Alright beautifly use silver wind," May said as she released beautifly from its pokeball. It was a huge success beautifly's silver wind was the best May had ever seen it. Beautifly was surrounded by beautiful sparkles. _

_"An amazing silver wind attack from May's beautifly," Marilyn said. "This will be hard to _beat folks,_ let's see what the judges give May for her fantastic performance." Nurse Joy, Raul Contesta, and Sukizo all gave May a ten. _

_"And it's a perfect score of thirty from the judges!" Marilyn said. Then the audience started cheering for May. _

_"May! May! May! May!" _Then May heard Ash's voice.

"May! Wake up May!" He said trying to wake her up.

"Yeah Ash, what is it?" May answered drowsily.

"Come with me, I have something to show you," he said grabbing her hand.

They quietly tip-toed through the hallway trying not to wake anyone, once they were out of the pokemon center Ash took May up onto the roof.

"Ash, what are we doing up here?" May asked confused.

"I thought it would be nice to sit up here and watch the sunrise together. I wanted to do something for you because you were feeling so bad yesterday."

"Ash you have got to be the sweetest boyfriend I've ever had." May said smiling.

"I thought that I've been the only boyfriend you've ever had." Ash said looking confused.

"I know but you know what I mean." May said winking at him.

"Um, not really n-," then he was cut off when May pulled his body closer to hers and pressed her lips up against his. Ash was shocked at first but then he relaxed and kissed her back. He put his arms around her waist and pulled her even closer. May ran her hand through Ash's hair; she could feel Ash breathing into her slightly parted lips. She let her tongue start to run up and down his mouth. They pulled apart after nearly five minutes and went to go meet everyone else for breakfast. \

"Okay guys," Brock asked. "What are your plans today? Are we going to spilt up or did you guys all want to stay together."

"Well I wanted to go around town with Ash today," May said.

"So they can kiss," Max said smiling deviously at his sister.

"No so he could also help me train."

"And kiss."

"And look around town," May said becoming enraged.

"While kissing," Max said.

"MAX! IF YOU DON'T STOP RIGHT NOW I SWEAR I AM GOING TO KICK YOUR" May screamed but was cut off when Ash put his hand over her mouth.

"Okay, you guys could do that and I was going to go shopping for supplies today." Brock said.

"Okay well could I come with you Brock," Miley asked.

"Sure anyone else want to come?"

"No I was also planning on training today." Ashley said.

"Yeah and I was going to help her," Lauren said.

"Could I come watch you Ashley?" Max asked.

"Of course you can Max," Ashley said.

"Alright now that we know what we are all doing for the day, let's meet back here at around 5:00," Brock said.

"Okay," everyone said in unison.

Ash and May were walking hand in hand down the sidewalk going from store to store and talking.

"So May when did you want to start training today?" Ash asked.

"Um I was thinking that we could go into a few more stores and then we can start training."

As they continued to walk down the street they were spotted by someone.

_Ooh cute boy alert. _Amber thought to herself as she saw Ash walking down the road.

"Oh May I just forgot I have some really important things I need to do today," Ash said. "So could I just meet you for training at the pokemon center at 3:00?"

"Yeah I guess so," May said confused and disappointed.

"Great thanks," he said as he ran in the other direction.

_Now is my chance. _Amber thought as she followed Ash. _Wait! I can't just go up to him I have to have a reason. I've got it! _

"Alright Azurill come on out," she said releasing it from its pokeball.

"Azu Azurill. (What is it Amber?)" It asked.

"I need you to stay here and act like I lost you." Amber said.

"Azurill? (Why?)"

"You'll see now will you do it for me?"

"Azu Azurill rill (You got it.)"

"Thanks."

Amber looked down the street and found Ash walking towards a jewelry shop. She ran up to him trying to catch up with him. She finally was close enough that she could touch him.

"Excuse me?" She asked. "Will you please help me?"

"Sure what's wrong?" Ash asked confused.

"It's my poor Azurill. I can't find her anywhere, she was my first pokemon and I don't know what I would do without her." Amber said fake tears forming in her eyes.

"Yeah of course I'll help you." Ash said.

"Thanks," Amber replied. "I last saw her over by the antique store but then I lost her."

"Okay lets start there then." Ash said as they ran in that direction.

They searched for twenty minutes trying to find Azurill. _Okay Azurill you can come out now. _Amber thought. No sooner Azurill came running towards Amber. It jumped into her arms and seemed ecstatic to see her trainer again.

"Oh Azurill! I'm so glad you're alright!" Amber said. Then she turned to Ash and hugged him. Ash blushed bright red but hugged her back. "Thank you so much for helping me."

"You're welcome. By the way my name is Ash and I'm a trainer from Pallet Town."

"Well Ash as payment for helping my find Azurill would you like to join me for lunch my treat."

"Sure thanks that would be great." _Wow she is really nice and pretty cute too. _Ash thought.

May looked at the clock tower, it was 3:30.

"Where is he? He was supposed to meet me here a half an hour ago." May said wondering where in the world Ash was. Just then a young man with brown hair was running towards May.

"Excuse me miss." He said.

"Yes," May replied.

"I'm sorry to bother you but I've been trying to find you all day. I found your bag in the department store downtown and I wanted to make sure you got it," he said.

"Oh well thank you I'm glad you found it. What's your name?"

"I'm Daniel Smith but you can call me Danny."

"Well thank you Danny for bringing this to me." May said. Then she glanced at the clock tower again.

"Are you waiting for someone?"

"Yeah my boyfriend," May said. "He said he was going to meet me here at 3:00 to help me train for the contest but I haven't seen him since this morning."

"Do you mean the Christmas Contest?" Danny asked.

"Yeah."

"Oh well I could help you train. I'm entering the contest too and I could use the practice. So would you like to have a practice battle with me?"

May thought about it for a minute. "Thanks Danny I would love to."

Ash and Amber spent the whole afternoon together hanging out around town and getting to know each other.

"Well Ash this has been a great afternoon. I hope I will see you again soon." Amber said giving Ash a good-bye hug and walked off.

Ash looked at his watch it was 5:00.

"Looks like I'm right on time," he said as he entered the pokemon center. "Hey Brock. Where's Miley?"

"Oh she went to go put her bags in her room and Max, Lauren, and Ashley are in there rooms too." Brock said.

"Where's May then isn't she here?"

"I thought you were with May." Brock said.

Ash then realized that he was so busy with Amber that he forgot all about May.

"Crap!" Ash said.

"What's the matter Ash?" Brock asked.

"I was supposed to meet May at 3:00 to help her train," Ash said as he ran out the door. _Oh no I have to find her. She's gonna kill me when she finds out that I forgot about her. _Ash thought. He was to busy thinking to watch where he was going and ran right into someone.

"Ouch!" Danny said as he and Ash both landed on the ground.

"Oh I'm sorry," Ash said getting up and helping Danny off the ground.

"Its okay dude I'm okay," Danny said. Then Ash heard a girl's voice.

"Danny are you okay I saw you fall." May said running towards them.

"May!" Ash said. "I'm so sorry I forgot about you today I promise I'll never do it again."

"It's okay Ash. Danny helped me train today so it's no big deal." May said.

"Well May I'll see you around." Danny said.

"Bye Danny." May said as she waved at Danny who waved back and disappeared over the hill. "Hi sweetie." May said as she kissed Ash.

"Wait so you're not mad at me." Ash said confused.

"No you're fine but don't ever do it again." May said.

"Alright I promise I won't. Come on let's go meet everyone inside."

So everyone meet in the pokemon center and went on to dinner and talked about there day and what everyone did. Then everyone went off to there rooms to go to bed. May woke up in the middle of the night.

"Ugh I can't get back to sleep. I'll go see Ash maybe he's awake too."

She quietly tip-toed out of her room so she didn't wake Max up. She came into Ash's room and saw him sleeping. _Ash is so cute when he's asleep. _

She quietly went over to him and gave him a kiss on the cheek. Then Ash spoke subconsciously.

"Mmm…Amber." May gasped. She went back to her room and sat on her bed. She knew that she was definitely not going to get any sleep that night.


	3. Chapter 3

Happy New Year everyone here is chapter 3! **Please Read and Review! **

Ash awoke the next morning feeling refreshed and ready to start the day. He showered got dressed and went down stairs where he saw that everyone else was already up.

"Hey Ash," Brock said. "We're gonna go grab some breakfast. Are you coming with us?"

"Brock we're talking about food. You've known me long enough to know the answer to that question." Ash said.

Everyone laughed except for May, she was still thinking about what had happened last night. She was still confused about how Ash could have even known Amber, he wasn't there when she met Amber at the contest hall. _I still don't get how he could have known Amber, it makes no sense. Wait! I never asked Ash what he was doing yesterday afternoon, maybe he and Amber met yesterday and he didn't tell me. Something must have happened between them yesterday if he dreams about her kissing him. _May was too caught up in her own thoughts that she didn't notice that Ash was staring at her.

"May are you okay you haven't said a word all morning," he said looking at her, he sounded concerned.

"Yes Ash I'm fine," she replied not looking at him.

"Anyways so I thought that we could do some training today since I wasn't there yesterday."

"Yeah, sure I guess that would be great," she said. Ash looked at her. _She seems really distracted today. I wonder why she's acting this way, maybe she lied to me yesterday, she probably really was mad that I was late yesterday._ "Guys I just rememberedI promised Danny that I would meet up with him this morning and I don't want to be late," she said as she grabbed her bag and started towards the door.

"May wait, I could come with you," Ash said.

"That's alright I think that it would be better if we were alone," then she ran out the door to go meet Danny.

"What's with this Danny guy, I don't trust him," Ash said as he watched May walk out the door.

"I don't think that you need to worry Ash," Lauren said. "They sound like they're just friends and there is no need for you to get jealous."

"Jealous! I'm not jealous, is it so wrong that I want to know about this guy that my girlfriend is with. Besides if they're just training then why do they need to be alone?" Ash asked.

"Well I can't answer that question for sure but still Ash you probably don't know the whole situation," Lauren said.

"Lauren's right Ash you probably don't know everything that's happening," Brock said.

_Oh I know what's happening,, what's happening is that Danny guy is trying to steal my girlfriend, well that's not happening not if I can help it! _Ash thought to himself then he stormed right out of the pokemon center trying to find May.

"Hey you guys have known Ash for a long time should we be worried," Max asked the others.

"Probably," everyone answered back.

May walked towards the hill where she and Danny planned to meet when she saw him sitting on a rock near the foot of the hill.

"Hey Danny, why are you sitting over here, I thought that we agreed to meet at the top of the hill like yesterday," May asked.

"I don't know I just felt like meeting you down here, but we could walk up the hill and train there if you want," he replied. May nodded in agreement and they started up the hill together. Danny glanced over at May and noticed that she seemed upset, her eyes looked hard and cold and her face was missing the glow that Danny had noticed yesterday. "Hey May, are you alright?" He asked.

"Yeah Danny I'm fine," she said, and then she let out a heavy sigh and looked back up at Danny. "No Danny I'm not fine, I'm actually very upset."

"Are you upset with me? Is it something I did?" He asked looking at her.

"No its not you it's my boyfriend," she said softly.

"Oh you're upset because of yesterday right, when he was late."

"I'm not upset that he was late, but I'm upset because of _why_ he was late," she replied.

"Why was he late?" He asked. Then May told him about what had happened last night. She told him about how Amber and their confrontation at the contest hall two days ago and how Ash was dreaming about Amber and how she thinks that Ash was late yesterday because he was with Amber.  
"Do you live here Danny?" She asked.

"Yeah ever since I was a baby."

"Well do you know anything about Amber Mason?" Then Danny looked at her, he had a look of disgust on his face.

"Oh yeah I've also known Amber since she was a baby. She was in my preschool class; she used to bite the heads off dolls."

"Why," May asked she looked scared.

"I don't know I think she just likes to destroy things."

"I don't know what Ash sees in her, she's just so mean," May said.

"Well that's weird because Amber is mean to everyone except for…" then his voice trailed off.

"Except for who…" May said dreading what he was about to say next.

"She's mean to everyone except for the boys that she likes… a lot," Danny said looking at May. May just sat there trying to make sense of what she just heard. _Amber likes Ash, she thought. _

"She can't like Ash," May said. "He's my boyfriend," May said then she slowly turned towards Danny. "I love him."

Ash was wondering outside the pokemon center trying to find where May had run off to. He was making himself crazy thinking about May running off with Danny and leaving him alone.

"Where could she be, this is a big town she could be anywhere," he said then he heard someone calling him.

"Ash, is that you?" He turned around and saw Amber running towards him.

"Oh hey Amber, what's up?"

"Not much since yesterday, what are you doing out here?" She asked.

"I could ask you the same thing," he replied grinning at her.

"Well I knew that you were staying here at the pokemon center so I walked down here to see if you might want to hang out with me today," she said. Ash thought about it for a moment. _Well I do like being around Amber, maybe I could find May while I'm with her. _

"Okay sure Amber that sounds great." They both walked over towards the hill where May and Danny were. Then Amber grabbed Ash's arm and spun him around so he was facing her.

"Ash could I ask you something?"

"Sure Amber what is it," he asked confused.

"Well you know about the Star Lighting Ceremony," she said. "Where the whole town comes together and lights the star on the tree, and they also honor the champion of the Christmas Contest."

"Yeah my friend Brock told my friends and I about it when we first came into town."

"Well I was just wondering if you would like to come to it with me, you know as my date," she said nervously.

Ash stood there looking at Amber nervously. _Oh no, I don't want to hurt her, but I'm May's boyfriend so I can't go with her. _

"Um Amber I'm sorry but I just can't, I have a girlfriend and I know that she would never cheat on me, I hope that we can still be friends." Then Ash looked up and saw two people near the top of the hill. It was May and Danny, they were talking, Ash kept watching and was shocked at what he saw next, May and Danny were kissing!

"Ash are you okay?" Amber asked.

"Yeah I'm fine, but I changed my mind I'd be happy to be your date for the ceremony."

"Great! So do you still want to hang out today," she asked. Ash looked back up at May and Danny, they were hugging now.

"I would love to," he replied then he grabbed Amber's hand and they walked away.

Danny and May continued to talk to each other for a few minutes and then they decided to start training for the contest that was coming up. While May and Danny were training Ash and Amber were spending the day together in downtown Gem City. Ash was happy to be with Amber but he was still thinking about when he saw May and Danny kissing earlier that day. _How could she do this to me? We were just fine until she met that Danny guy. I knew something was going to happen, I just knew it! I thought she loved me…but I guess I was wrong. _

After a long day of training and talking May and Danny made their way back to the pokemon center.

"Thanks Danny for being such a good friend today," May said hugging him.

"Your welcome May, if you need me for anything just call me okay."

"I will thanks Danny." May said, and then she heard voices that she recognized, one was a boy's voice and the other voice belonged to girl. She looked behind her and saw that it was Ash and Amber. _What is he doing with her?! That little tramp is trying to steal my boyfriend from me. I knew something was going on with them. _Ash looked towards the pokemon center and saw May and Danny standing near the door. _Now is my chance. _Ash thought.

"So Ash did you want to hang out again tomorrow," Amber asked.

"Yeah that would be great," he said. Amber turned to walk away and then Ash grabbed her arm and pulled her into a kiss, Amber was shocked at first but then she closed her eyes and kissed him back.

May turned around to look at Ash and Amber again and was horrified at what she saw.

"May are you okay?" Danny asked. May didn't speak she just pointed in the direction she was looking. "Oh no."

May eyes were filled up with tears, she thought that witnessing Ash dream about kissing Amber was bad, but witnessing him actually doing it was much, much worse.


	4. Chapter 4

Chapter 4

Ash walked into the pokemon center and saw May staring at him heatedly.

"Ash Ketchum!" She yelled. "I need to speak to you, NOW!"

Ash just stood there and looked at her blankly.

"About what?"

"About what? I want to talk to you about kissing another girl that's what!" "I thought you loved me!"

Ash looked at her with anger in his eyes. "Well May I would really like to talk about you kissing another guy."

May just stood there looking at him nervously. "I-I don't know what you're talking about." She said.

"Don't lie to me, I know about you and Danny I saw you two kissing earlier today," he looked at her and spoke again. "So tell me May how can you be mad at me when you did the same thing." Then Ash heard someone walking up behind him.

"You don't know the whole story Ash," the person said. Ash turned and saw Danny standing behind him. "Here's what happened…

Flashback

"She can't like Ash," May said. "He's my boyfriend," May said then she slowly turned towards Danny. "I love him," after saying that her eyes started to fill with tears. "I don't understand, things were going so well with us."

"May," Danny said putting his arm around her. "Please don't cry, I can tell that you love Ash and I bet he loves you to, and you may not know what's happening between them. I promise I'll help you get Ash's mind, and his love back to you."

"Thanks Danny, I feel like you're the only person I can count on right now," she said and then she gave Danny a kiss on the cheek. He sat there silently with a small blush on his cheeks. May started to move her face closer to his, then May suddenly pulled him into a kiss, Danny kissed her back for a few seconds and then pulled back.

"May I'm sorry I can't do this, it would be wrong of me to take advantage of you while you're so vulnerable. Trust me Ash loves you and we just have to remind him!"

"Thanks Danny you really are a good friend," May said as she pulled him into a hug.

End of Flashback

"So Ash that's what really happened," Danny said.

"So you admit to kissing my girlfriend," Ash said looking at him with cold eyes.

"Yes and I'm sorry but it won't happen again." Danny looked at Ash hoping that he would accept his story and apology and everything would be normal again. May looked up at Ash, he had a blank look on his face so she had no idea what he was thinking.

"Ash," she said walking closer to him. "I'm sorry about what I did earlier today and I hope you can forgive me."

Ash just looked at her his eyes started to water.

"I'm sorry May, but if you can go and kiss another guy like you did I don't think there is much hope for us." Then he said the five most painful words. "I'm sorry May but, I'm breaking up with you."

I'm sorry to end this chapter so sadly but this just makes the story all the more interesting and easy to read to see if Ash and May will get back together. So please **READ AND REVIEW!!! **

P.S I'm sorry that this chapter is so short. 


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